
Pet-friendly holiday rentals in Big Pine Key
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Top-rated pet-friendly home rentals in Big Pine Key
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Pet-friendly house rentals

Waterfront Escape -VACA-23-408
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys
Thank you so much for such an amazing stay! We loved the gorgeous property and all the lovely decor inside! Property was extremely clean and Sandy was so kind and helpful! We spent almost every evening in the hot tub! The home had everything we neded for an awesome week and was in a great central location, close to everything we wanted to do! We loved TJs Tiki Bar for dinner and a beautiful sunset! Thank you again Sandy! :)

The Toasted Coconut-Pool-Bikes-Grill-Chic!
We loved The Toasted Coconut! Everything about our stay was amazing but what made it above and beyond any place I've ever stayed, were the added accommodations. Since we flew from out of state, we were very limited on the things we could bring. Katie had a high chair and pack and play ready for my little one upon arrival! This was extremely helpful and definitely took some stress off our shoulders! Not to mention, made life easier for our 1 year old! Thank you Katie and Cody for welcoming your home to us!

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
We all had a great time and the house was gorgeous! The house had everything we needed for a pool day or a fishing day. The location is great and has everything you need around. The host even sent key lime pies from Sweet Savannah’s (walking distance) as a sweet gesture after needing a few people to stop by to fix something outside. We can’t wait to stay again!

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

Spacious lux home, private pool/spa, 80' dock
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!

Paradise found
The house was clean and a great option for traveling as a large group. It was away from the bustle of Key West, but still easy to get around, and the restaurants nearby are delicious.

Water, Water Everywhere! "The Wheel House"
My parents, wife, and I booked a three day run at this spot. It was awesome! The location was perfect and Leila recommended a lot of places around to visit and eat. Fishing is active off of the back dock and most of the surrounding areas have lights set up, so there were plenty of fish to target all day. It is a quick drive to Key West and had some nice beaches within a 5 minute drive. One big plus is that the cut that this home is located on had minimal seaweed compared to most of the other areas. Overall, this is the perfect spot. We will definitely be back.
Pet-friendly home rentals with a pool

Turtle Cove Views at Venture Out
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.

Sombrero beach oasis, great location, many amenities
Incredible for a family vacation. 🏝️The property feels very private, clean, well decorated, and many amenities. We tried out the paddle boards and spent a lot of time in the pool. When going to the beach, Aileen already had chairs and towels to bring! This property really is a gem. Thank you Aileen!

Ocean Front Home in Great Location
Fantastic place for a home base while the beautiful keys. Close enough to key west for an upbeat day, very quiet in the evening. If anything, I’d say I was expecting less from the description and was very surprised at how nice this place is. I would stay here again in a heartbeat!

Paradise Cove!30ft Dock Pool BBQ
Had a great week at Yunis place! Her house was extremely clean and had everything we needed and more especially for cooking which was nice. She had probably the most comfortable bed, sheets and pillows I’ve ever used. I loved how it was clutter free and didn’t have any breakable decorations down low around since we had our two toddlers with us. The pool was the perfect size for us and it was great to relax outdoors. We even saw Manatees swim up to the dock. 10/10 would recommend this spot.

Waterfront 2-bedroom Home w/Pool and Spa
Great place! Exactly like the pictures. AMAZING heated pool! Very clean. Ruth was an excellent host! She had fresh flowers, toiletries and even snacks and breakfast items to get us started! Most Airbnb’s you have to provide your own TP, paper towels, trash bags and soap but not here! Ruth had the place very well stocked. We will definitely be returning! Thanks for a memorable Thanksgiving week Ruth!!

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Our family of five adults, plus two additional relatives, had the most incredible stay at this property. While we had planned several excursions, we found ourselves spending the majority of our seven-day trip enjoying everything this place had to offer. From fishing off the dock to kayaking and paddleboarding, the outdoor amenities were top-notch. The pool area was the perfect spot for relaxing and spending quality time together. One of the standout features was the amazing outdoor freezer—ideal for storing our fresh catch of Mahi from our charter trip. Inside, the kitchen was impressively well-equipped, making cooking a breeze. Every detail of the home was thoughtfully curated to provide comfort and convenience. This stay exceeded our expectations, and we’re already looking forward to returning. Highly recommend for anyone seeking a well-appointed, adventure-filled getaway!

Waterfront Private Home w/Pool-Family&Pet Friendly
The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.

Boater’s Paradise 3br/2.5ba at Coral Lagoon
Larry was an excellent host who did everything to make the stay enjoyable. I would highly recommend staying at Larry's place and will definitely stay again if in the Marathon area.
Private, pet-friendly home rentals

Coral Lagoon #23- Private Villa Home
We had a great stay. Although it was not on the beach, it was a short drive to Sombrero Beach and not very far from Bahia Honda. The pool was lovely and our grandsons loved it.

Castaway Cove: Pet-friendly 2/2 condo near beach!
Nice cozy spot while visiting Key West.

Seaside Sunrise. Newly remodeled waterfront
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
We had a great long weekend at Alex house! You are provided with a starter kit, so you may need to buy extra supplies if planning to stay in at property. House vibes are very keywest. Winn Dixie very close and Bahia Honda state park was close by and beautiful to spend the day if looking for something to do. Keywest about 40 min drive, easy to get around. Had plenty of blankets, pillows and accommodated 10 of us— we did bring an air mattress which I would recommend as sofa beds are not the most comfortable. Has a beautiful backyard which we spent a lot of time on and yummy walkable restaurant. Plenty of parking. Host was very responsive and checked in with us to make sure check in was smooth.

Waterfront Cottage Walk to World Famous Lorelei
What an amazing place! My wife and I have stayed in Airbnb properties all over the world, and this was one of our favorites. Exactly as described. Very clean, safe, and comfortable. The location and layout of the property is absolutely perfect and private. This was our first time to Islamorada and this place made it an even better experience. We had a manatee sighting and the deck over the water was my favorite part. Perfect place to have a drink and watch the sunset. If you are planning a trip to the keys, do yourself a favor and stay here.

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
Regina and Captain Rob were great hosts! They gave us local recommendations and communicated well! We had such a great time using the tiki bar and the pool. It was our first trip with our baby and the place even had a crib for us to use. Would definitely return!

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club
Amazing location, great house with lots of space, cute artistic touches and we really appreciated the sharp knives! The screened in lanai was fantastic! Highly recommend! We’d come back in a heartbeat!

Oceanview Oasis! Screened Porch & Outdoor Theater
The home was beautiful, clean, well stocked, and comfortable. It had everything we could possibly need and more. The beds were comfortable and the couch was huge and cozy. The view is spectacular, we spent every morning out on the patio with our coffee. The property is in the perfect location as well, making everything in Marathon no more than 8 minutes away. It was the perfect get away for our little family (fur baby included).
Quick stats about holiday rentals that are pet-friendly in Big Pine Key
Total rentals
120 properties
Nightly prices starting at
₹5,147 before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
100 properties are a good fit for families
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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